Electrochemical Transformation of Malononitrile and Carbonyl Compounds into Functionally Substituted Cyclopropanes: Electrocatalytic Variant of the Wideqvist Reaction

✍ Scribed by Michail N. Elinson; Sergey K. Feducovich; Tatiana L. Lizunova; Gennady I. Nikishin

• Book ID: 104202626
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 169 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00195-2

✦ Synopsis

AbstractÐElectrolysis of malononitrile and carbonyl compounds in the presence of alkali metal halides in an undivided cell results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 60±90% yield. This electrocatalytic variant of the Wideqvist reaction using malononitrile instead of bromomalonitrile was successfully performed. Electrocatalytic transformation of substituted 1,1,2,2-tetracyanocyclopropanes in methanol or ethanol in an undivided cell leads to substituted 2-amino-4,4-dialkoxy-1,5-dicyano-3-azabicyclo[3.1.0]hex-2enes in 70±95% yields after 0.05±0.10 F/mol of electricity has been passed.